3:30 because I'm new and didn't see the requirement deadline to buy badges on Feb 11.  I just kept seeing Feb 13 dates all over the place for housing registration.

It's on the guide page, but it isn't at the top where it should be.  Newcomers are kind of screwed.

They're already out of downtown hotels.
How do we check for new openings in the downtown hotels in the weeks to come?

Being prepared to likely NOT getting something downtown
with 12:52 EST queue, I'm not surprised that I didn't. 

I booked my "contingency" room after last years Con.

All available rooms will show up. You can do this anytime before July 18th.

If you have an existing reservation it will stay intact as long as you do not book a new one.

Looks like I've got a new hobby.

Always good to look, but some of the best times I've found are

1.  Event day - People rage quit Gencon if they don't get any events
2.  The day of cancelling hotels before getting hit with a cancellation fee

This year there will probably be a decent amount of activity when Gencon announces the final health policy for Gencon.

My buddy had 12:06, and we got a room at the Westin. My time was 1:40, and I managed to get a suite 6 blocks away, for some friends who are attending, but haven't organized fully who/which are going. 

GENCON!!!!!!!!!!!

Again, Good Fortune in your Quest, brave adventurer!

This kind of optimism is fascinating to me.  No one is able to sit on the hotel portal all day long to see if someone drops a reservation between now and August.

The odds of just randomly being on to check and see someone dropped before someone else gets the opening is so slim, it'd be like the hotel lottery.

And new properties aren't going to be opened by August.  That takes much longer than 6 months, and there are no hotels in downtown that are currently in development that will be open by August.

Hotels downtown have been sold out now already.  Anyone saying 3:30 would have a chance are being ridiculous.
 

You don't have to be actually watching the Housing Portal tab all day. What I usually did in past years was keep it open, then refresh it whenever I had a break in whatever else I was doing. Got a downtown room every year that way. And I don't even work with a PC at my day job, so this was all on my off-time.

It's 6 months between now and GenCon.  If I'm not on it every day, there's no way of knowing when a room becomes available.  Meanwhile there are plenty who are desperate enough to be on here a lot more often and snag them quickly after they become available.

Whether I randomly check throughout a day or not, it could be weeks or months before I catch something at the same time I'm on.

Sold Out Advisory!
Sold out inventoryDue to unexpected turnout, the Gen Con 2022 attendee room block has sold out. Over the coming days and weeks we’ll be procuring supplemental inventory and making it available for booking on a first-come first served basis. If you were unable to obtain a hotel room on opening day or are looking to change your assigned hotel or room type, please check back periodically as inventory will become available through supply additions and booking cancellations. Thank you for your attention and patience.

HAHAHAHAHA Jesus Christ, "unexpected" and they still bother to give people false hope of putting them at the back of the line like they have a chance to get a hotel.

And by the time it came for me, everything was out at the airport. I'm driving in from Columbus, Ohio, so if I have to drive in every day, I'd prefer to stay on the East side of Indy. So already made my reservation at the usual place.

Even AirBnB and temp-Condos are sky high prices.  I have only found a few that were under $250/night.  Most are $400-1000/night plus they add now $100+ fees to that

3:30pm housing portal time. Everything is sold out, so that's cool I guess

Secondly, 3:30 ain't working this year, it is true.  But, considering there was still downtown availability at that time last year, I wouldn't call anyone who considered that likely to be "ridiculous".  

In my opinion, it was very difficult to predict demand for 2022 because there are so many factors at play.  No clue how many rooms were in the block, but if it was relatively the same, then demand pressure on the housing portal seems to be at near 2019 levels.

For the record, my time was 3:07...my wife's was 3:08.  :) 

I know that in another thread I advised fiddlemaster that 3:30 was not the end of the world - and that there would be hotels still available.  This is the first time I've ever seen hotels sell out completely on opening day - let alone in just over 2 hours.  So...yep...looks like you were right fiddlemaster.  This is unprecedented - and I suspect that maybe hotels did not offer as many rooms to the portal this year because so munch inventory went unsold last year. Gen Con may be working with the hotels that are part of the block to maybe expand the number of rooms they have on offer to the Housing Portal.  That seems like the first step to increasing supply.  

However, as others have noted - there are 6 months until Gen Con.  I've never *not* gotten a downtown hotel when I wanted one and I'm not sitting at my computer refreshing all day long for months (and I do work from home and am on a laptop; but I'm *working* not watching the Gen Con Housing Portal).

What has worked for me:

1. I book whatever hotel I can get around the Indianapolis area - in block or out.  You don't need a downtown hotel to have a great Gen Con.  Done it multiple times; is it different? Of course - but if your entire Gen Con experience is built on a downtown hotel you're going to be disappointed often.  There is just too much demand for a limited supply.
   
2. I check the portal before I go to work, I check at lunch time, I check when I get home/get off of work and, sometimes, I check before I go to bed.  That's it.
   
3. I am aware of cutoff dates - just after event registration, just before badge registration, just before room cancellation dates and, if I'm able, I add a few checks into the day (maybe on breaks).
   

Good luck.